Ask how many units they manage and how much experience they have.

Within my 20 years of experience, owning 30 properties and managing over 300, I've found that the question always comes down to this: Can you do better than the rate you're paying—either by saving more or making more?

Selling and exploring a 1031 exchange could make sense if you can find a deal with stronger cash flow or faster equity growth, but the key is comparing your current return to what your skill and experience could generate in another investment.Here to help,Jorge

In most cases, I don't recommend renting out your primary residence especially if you have no rental experience and that is because usually your primary residence was bought without the idea of renting it out.  

I've read mixed reviews on host experiences with VRBO and Booking.com, so I've been hesistant to list there.Currently, using PriceLabs and tweaking/ analyzing pricing a few times a week.Honestly, my photos are not the greatest yet, but it is a high priority for me to get professional photos soon.

Becoming a real estate agent is a good idea to gain experience, but you could also explore property management, wholesaling, or working with an investor to build your network. 

Having no experience is risky.

I understand that starting condition and location will play a factor here, but just wondering what your experience has been.

I think the before vs after pictures really speak primarily to your experience and ability to execute a project so it can help lenders gain comfort with future projects and allow you demonstrate what level of detail you except out of your contractors.

@Anthony MillerYour property management experience is a major advantage as you start investing, giving you a head start with tenant screening, lease agreements, and maintenance coordination.